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ETHYL DIGLYME
CAS No. : 112-36-7
EC No. : 203-963-7
Synonyms:
Diethylene glycol diethyl ether; Diethyl carbitol; Bis(2-ethoxyethyl) ether; Ethyl diglyme; Diethyldiethylene glycol; 3,6,9-Trioxaundecane; Diethyldiglycol; 1-Ethoxy-2-(2-ethoxyethoxy)ethane; DGDE; DIETHYLENE GLYCOL DIETHYL ETHER; 112-36-7; 2-Ethoxyethyl ether; Diethyl carbitol; 1-Ethoxy-2-(2-ethoxyethoxy)ethane; Ethyl diglyme; Bis(2-ethoxyethyl) ether; Diethyldiethylene glycol; 3,6,9-Trioxaundecane; Ether, bis(2-ethoxyethyl); DEGDEE; Ethane, 1,1'-oxybis[2-ethoxy-; 2-(2-Ethoxyethoxy)-1-ethoxyethane; Diethylether diethylenglykolu; Ethyl Diglyme; 1-Ethoxy-2-(beta-ethoxyethoxy)ethane; HSDB 68; UNII-ZH086O935Z; Ethanol, 2,2'-oxybis-, diethyl ether; Ethane, 1,1'-oxybis(2-ethoxy-; Glycol, diethylene-, diethyl ether; EINECS 203-963-7; Diethylether diethylenglykolu [Czech]; ETHYL DIGLYME; diethyleneglycol diethyl ether; AI3-19428; CHEBI:44664; ZH086O935Z; Ethanol, 2,2'-oxybis-, diethyl ether; Ethyldiglyme; Hisolve EDE; 2-Ethoxyethyl ether, 98+%, extra pure; P4G; Ethyldiglyme; ethoxyethyl ether; (1-ethoxy)-ethyl ether; diethyleneglycoldiethylether; DSSTox_CID_5047; ACMC-2099ei; EC 203-963-7; diethyleneglycol diethylether; 1,5-diethoxy-3-oxapentane; DSSTox_RID_77639; DSSTox_GSID_25047; SCHEMBL16596; Diethylene glycol diethylether; KSC174Q2J; 1,1'-oxybis(2-ethoxyethane); CHEMBL1235106; Diethylene glycol, diethyl ether; ETHYL DIGLYME; ZINC2041052; Ethane, 1,1'-oxybis[2-ethoxy-]; Tox21_302050; 1-ethoxy-2-(2-ethoxyethoxyl)ethane; 7998AF; ANW-16456; LS-552; 1-ethoxy-2-(2-ethoxyethoxy)-ethane; AKOS015915322; 1-Ethoxy-2-(2-ethoxyethoxy)ethane #; Ethyl Diglyme; DB08357; 1-Ethoxy-2-(.beta.-ethoxyethoxy)ethane; NCGC00164135-01; NCGC00255128-01; CAS-112-36-7; SC-76795; B0489; Diethylene glycol diethyl ether, HPLC Grade; FT-0624903; Diethylene glycol diethyl ether, for HPLC, >=99%; J-509308; Q5275148; Diethylene glycol diethyl ether, reagent grade, >=98%; F8881-4182; Diethylene glycol diethyl ether, Vetec(TM) reagent grade, 98+ %; 2-ethoxyethyl ether; 112-36-7; Diethyl carbitol; 1-ethoxy-2-(2-ethoxyethoxy)ethane; DGDE; Ethyl diglyme; Bis(2-ethoxyethyl) ether
Ethyl Diglyme
Diethylene glycol diethyl ether (Ethyl Diglyme) is an organic solvent with a high boiling point.
Properties
Chemical formula C8H18O3
Molar mass 162.22 g/mol
General description
Ethyl diglyme is a hydrophilic[10] electron-donor solvent.[7]
Application
Ethyl diglyme may be used as a solvent in the following processes:
• Synthesis of 3,5-dinitrobenzaldehyde via reduction of 3,5-dinitrobenzoyl chloride using lithium aluminum tri-tert-butoxyhydride.[9]
• Copper-catalyzed cross-coupling of iodoarenes with 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine to form the corresponding trifluoromethyl arenes.[11]
• Conversion of olefins (for eg: (±)-α-pinene) to primary amines (3-pinanamine) via hydroboration-amination reaction.
The present invention provides a method of producing glycol ethers, which are also commonly known as glymes. The method according to the invention includes contacting a glycol with a monohydric alcohol in the presence of a polyperfluorosulfonic acid resin catalyst under conditions effective to produce the glyme. The method of the invention can be used to produce, for example, monoglyme, ethyl glyme, diglyme, ethyl diglyme, triglyme, butyl diglyme, tetraglyme, and their respective corresponding monoalkyl ethers. The present invention also provides a method of producing 1,4-dioxane from mono- or diethylene glycol and tetrahydrofuran from 1,4-butanediol.
Diethylene glycol and ethanol react in accordance with the method of the invention to produce diethylene glycol diethyl ether (ethyl diglyme). These two reactants also produce diethylene glycol monoethyl ether, which is also known as “Ethyl CARBITOL®”.
Applications
Ethyl diglyme is used as a solvent in organic reactions due to its stability towards higher pH and its high boiling point. It is particularly involved in reactions utilizing organometallic reagents such as Grignard reactions and metal hydride reductions. It is also a solvent for hydroboration reactions with diborane.
Solubility
Miscible with water, ethanol, acetone, acetic acid, glycerine, pyridine and aldehydes. Slightly miscible with ether.
Notes
Hygroscopic. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
About Ethyl diglyme
Ethyl diglyme is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Ethyl diglyme is used in articles, in formulation or re-packing, at industrial sites and in manufacturing.
Article service life
Release to the environment of Ethyl diglyme can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites and as processing aid. Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials). Ethyl diglyme can be found in complex articles, with no release intended: vehicles. Ethyl diglyme can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).
Formulation or re-packing
Ethyl diglyme is used in the following products: laboratory chemicals and polymers.
Release to the environment of Ethyl diglyme can occur from industrial use: formulation of mixtures, manufacturing of the substance, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
USES at industrial sites
Ethyl diglyme is used in the following products: laboratory chemicals, pharmaceuticals and polymers.
Ethyl diglyme is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.
Ethyl diglyme is used for the manufacture of: chemicals, plastic products and electrical, electronic and optical equipment.
Release to the environment of Ethyl diglyme can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Manufacture
Release to the environment of Ethyl diglyme can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Category
Glycol Ethers (Glymes)
Description
Clear liquid with a pleasant odor; [CAMEO]
Sources/Uses
Used as a solvent and chemical intermediate; [Merck Index] Used in the coating industry and in photolithography to make semiconductor chips; Also used in adhesives, sealants, and automotive care products; [Reference #1]
Comments
Toxic after ingestion; [CAMEO] A reproductive toxin in experimental animals; [HSDB] A possible human reproductive toxin based on animal testing; A skin, eye, and respiratory tract irritant; [ICSC] Low acute toxicity to mammals but evidence of developmental toxicity and toxicity to blood forming organs in repeated-dose animal testing; A potential reproductive toxin; [Reference #1] Labeled as "May impair fertility" and "May cause harm to the unborn child" by EU regulations
Ethyl diglyme, or bis(2-methoxyethyl) ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. (The name "Ethyl diglyme" is a portmanteau of "diglycol methyl ether.") It is a colorless liquid with a slight ether-like odor. It is miscible with water as well as organic solvents.
It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.
Solvent
Structure of [Na(Ethyl diglyme)2]+ as found in its salt with the fluorenyl anion.
Because of its resiliance to strong bases, Ethyl diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.
Ethyl diglyme is also used as a solvent in hydroboration reactions with diborane.
It serves as a chelate for alkali metal cations, leaving anions more active.
Safety
The European Chemicals Agency lists Ethyl diglyme as a Substances of Very High Concern (SVHC) as a Reproductive Toxin.
Analyte: Ethyl diglyme; matrix: urine; procedure: gas chromatography with flame ionization detection
A monitoring method based on solvent extraction of adsorbed target glymes followed by gas chromatograph-mass spectrometry GC -MS analysis was developed for ... Ethyl diglyme. The best recoveries of target glymes were achieved when using a combination of sample collection medium of graphitised carbon black (GCB) with a solvent mixture of methylene chloride and methanol (95/5, v/v). Method detection /limit was/ ... 1.5 microg/cu m for Ethyl diglyme ... . Using this method ... Ethyl diglyme /was/ ... detected and measured successfully in diluted vehicle exhausts in diesel fuel engine tests.
Acute Exposure/ The compound was tested externally on the eyes of rabbits, and, according to the degree of injury observed after 24 hours, rated on a scale of 1 to 10. The most severely injurious substances have been rated 10. Ethyl diglyme rated 3 to 4 on rabbit eyes.
Developmental or Reproductive Toxicity/ Fifty pregnant CD-1 mice were given 3,000 mg/kg/day of Ethyl diglyme in water by gavage on days 6-13 of gestation and allowed to deliver. The test agent reduced maternal weight gain but had no effect on the offspring of treated animals.
Ethyl diglyme (DGDE) was evaluated for developmental toxicity in timed-pregnant CD-l mice. Ethyl diglyme was administered daily in distilled water by gavage at 0, 300, 1,500, 3,000 and 4,500 mg/kg on gestational days (gd) 6 through 15. Maternal toxicity was evident in dams exposed to Ethyl diglyme at doses greater than or equal to 1,500 mg/kg/day . CNS function was highly sensitive to treatment as evidenced by ataxia, coma and lethargy in a majority of the dams dosed. Mortality among confirmed--pregnant animals occurred with incidences of 0% (0/29), 0% (0/24), 8.6% (3/35), 11.8% (4/34) and 100% (14/14) in the control through high-dose groups, respectively. Deaths occurred early during the dosing period (gd 6-9), and all deaths at the high dose were preceded by evidence of severe CNS depression. There were no effects of treatment on any of the parameters that indicate changes in the numbers of resorptions, nonlive implants, fetal deaths as well as live fetuses. Average fetal body weight per litter was significantly lower at 3,000 mg/kg Ethyl diglyme when compared with the control group. The incidence of major malformations was low in all groups and was dose independent. The 1,500 mg/kg/day dose was a no observed effect level (NOEL) for developmental toxicity. In conclusion, development of the CD-1 mouse is not sensitive to Ethyl diglyme administered by gavage at maternally nontoxic doses. A NOEL for Ethyl diglyme-induced developmental toxicity was 1,500 mg/kg/day, a dose which produced maternal CNS depression and lethality (8.6%). The lowest dose given, 300 mg/kg/day, represented a NOEL for Ethyl diglyme-induced maternal toxicity.
Ethyl diglyme (DGDE) was evaluated for developmental toxicity in artificially inseminated, New Zealand White rabbits. Ethyl diglyme was dissolved in distilled water to provide doses of 0, 50, 200 and 400 mg/kg, and subsequently administered daily by gavage from gestational days (gd) 6 through 19. DGDE treatment did not adversely influence maternal viability. The only exception was that one of the 27 confirmed pregnant dams (3.7%) in the 400 mg/kg group died on gd 15. Necropsy of that animal indicated that its death was related to Ethyl diglyme exposure. The pregnancy incidence was similar across dose groups and ranged from 85.7% to 88.6%. Clinical signs of toxicity were observed during treatment with the greatest occurrence in the high dose group. Ataxia, coma, dyspnea and postdosing vocalization predominated at 400 mg Ethyl diglyme/kg/day. Weight loss (greater than or equal to 150 g/day) occurred in both the control and treated animals. Maternal body weight was similar among dose groups on gd 0 as well as throughout the treatment and post-treatment periods. When weight gain was compared, however, dams exposed to 400 mg Ethyl diglyme/kg had significantly lower weight gain than controls during the treatment period. Liver and gravid uterine weights did not differ among dose groups. There was no effect of treatment on embryo viability. The incidences of resorptions and fetal deaths were similar among the treatment groups. In addition, the number of live fetuses per litter and average fetal body weight per litter (both sexes) were not affected by Ethyl diglyme treatment. Nonetheless. when fetal body weights were analyzed by sex, female weight manifested a significant decreasing trend which was related to the statistically nonsignificant, weight reduction in the 400 mg/kg/day dose group, In addition, embryo/fetal morphogenesis was not observably altered by Ethyl diglyme treatment, based on the findings of external, visceral and skeletal examinations of gd 30 fetuses. In conclusion, embryonic and fetal development of the NZW rabbit was not sensitive to Ethyl diglyme as tested in the present study at maternally toxic doses. Although clearcut developmental effects were not identified for Ethyl diglyme, the significant decreasing trend in body weight of female fetuses at 400 mg/kg/day is marginal evidence of Ethyl diglyme-induced developmental toxicity. Since maternal toxicity was also observed at the high dose, the 200 mg/kg/day dose represents a no observed effect level (NOEL) for both Ethyl diglyme induced developmental and maternal toxicities.
An oral teratogenicity was conducted with 50 pregnant Charles River (CD-1) mice administered Ethyl diglyme (bis(2-ethoxyethyl) ether) by oral gavage at a dose level of 3000 mg/kg body weight on gestation days 7 to 14. The dose level chosen was the LD10 calculated from a previous range finding study. Mortality not was observed. Fetal toxicity was evident by statistical differences in number of dead pups per litter, and reduced pup birth weight (by analysis of variance). No significant changes were observed in number of pups per litter, percent pup postnatal survival, and pup weight gain over days 1-3 post partum. Of the pregnant mice, 95 percent of litters were viable. Gross necropsy observations were not reported.
Ethyl diglyme's production and use as a high boiling reaction medium, and as a solvent for nitrocellulose, lacquers, resins, and organic syntheses may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.52 mm Hg at 25 °C indicates Ethyl diglyme will exist solely as a vapor in the atmosphere. Vapor-phase Ethyl diglyme will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 14 hours. If released to soil, Ethyl diglyme is expected to have very high mobility based upon an estimated Koc of 39. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole. Ethyl diglyme may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation of Ethyl diglyme is not expected to be an important fate process in soil or water based on biodegradation studies conducted with sewage seed. If released into water, Ethyl diglyme is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to Ethyl diglyme may occur through inhalation and dermal contact with this compound at workplaces where Ethyl diglyme is produced or used. Monitoring data indicate that the general population may be exposed to Ethyl diglyme via inhalation of ambient air, ingestion of drinking water, and dermal contact with this compound and other products containing Ethyl diglyme.
Ethyl diglyme's production and use as a high boiling reaction medium(1), and as a solvent for nitrocellulose, lacquers, resins, and organic syntheses(2) may result in its release to the environment through various waste streams(SRC).
Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a log Kow of 0.39(2) and a regression-derived equation(3), indicates that Ethyl diglyme is expected to have very high mobility in soil(SRC). Volatilization of Ethyl diglyme from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole(SRC), derived from Its vapor pressure, 0.52 mm Hg(4), and water solubility, 1X10+6 mg/L(5). Ethyl diglyme may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation of Ethyl diglyme is not expected to be an important fate process in soil based on biodegradation studies conducted with sewage seed(6-7).
Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a log Kow of 0.39(2) and a regression-derived equation(3), indicates that Ethyl diglyme is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.52 mm Hg(4), and water solubility, 1X10+6 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation of Ethyl diglyme is not expected to be an important fate process in water based on biodegradation studies conducted with sewage seed(8-9).
According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Ethyl diglyme, which has a vapor pressure of 0.52 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase Ethyl diglyme is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(3).
An aerobic biodegradation study using gram-negative asporogenous rod bacterium isolated from soil by enrichment on triethylene glycol exhibited borderline growth (scarcely detectable growth, not reproducible) with Ethyl diglyme(1). In a screening study using a sewage seed, Ethyl diglyme (concentration not specified) had a 10 day BOD of 0.10 g/g (4.2% theoretical BOD) at 20 °C(2). Ethyl diglyme had a 21.7% COD removal at 30 °C from a starting concentration of 600 mg COD/L (time period not given) indicating little degradation compared to 95% degradation of ethylene glycol monophenyl ether(3).
The rate constant for the vapor-phase reaction of Ethyl diglyme with photochemically-produced hydroxyl radicals is 2.7X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). The rate constant for the reaction between photochemically produced hydroxyl radicals in water and Ethyl diglyme is 3.2X10+9 L/mole-sec(2); assuming that the concentration of hydroxyl radicals in brightly sunlit natural water is 1X10-17 M(3), the half-life would be about 250 days(SRC).
An estimated BCF of 3 was calculated in fish for Ethyl diglyme(SRC), using a log Kow of 0.39(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of Ethyl diglyme is estimated as 39(SRC), using a log Kow of 0.39(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that Ethyl diglyme is expected to have very high mobility in soil.
The Henry's Law constant for Ethyl diglyme is estimated as 1.1X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 0.52 mm Hg(1), and water solubility, 1X10+6 mg/L(2). This Henry's Law constant indicates that Ethyl diglyme is expected to be essentially nonvolatile from water surfaces(3). Ethyl diglyme's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Ethyl diglyme may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Ethyl diglyme has been qualitatively identified in drinking water(1). Ethyl diglyme was qualitatively detected in drinking water from Cincinnati, Ohio(2).
Ethyl diglyme has been qualitatively identified in ground water from the Hipps Road Landfill in Jacksonville, FL(1).
Ethyl diglyme has been qualitatively identified in trench leachates from Maxey Flats and West Valley low-level radioactive waste disposal sites(1). Ethyl diglyme has been qualitatively identified in advanced waste treatment water from Lake Tahoe, CA, Pomona, CA, and Blue Plains, Washington, DC(2). Ethyl diglyme was tested from a light duty truck using different fuel types; diesel mixed with Ethyl diglyme: cold start 79 ug/cu m, hot start 52 ug/cu m; diesel fuel: cold start 23 ug/cu m, hot start 25 ug/cu m; diesel fuel mixed with diethylene glycol dimethyl ether: cold start 7.7 ug/cu m, hot start 7.3 ug/cu m; diesel fuel mixed with 2-ethylhexyl nitrate: not detected for cold and hot start(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,489 workers (2,128 of these are female) are potentially exposed to Ethyl diglyme in the USA(1). Occupational exposure to Ethyl diglyme may occur through inhalation and dermal contact with this compound at workplaces where Ethyl diglyme is produced or used(SRC). Monitoring data indicate that the general population may be exposed to Ethyl diglyme via ingestion of drinking water(SRC).
Ethyl diglyme, also called diethylene glycol di-n-butyl ether, is a polar aprotic solvent with excellent thermal and chemical stability. Ethyl diglyme, or glycol diethers, are a widely used family of saturated polyethers for increasing anion reactivity in a given system, thus affecting selectivity and reaction rates. Ethyl diglyme is one of the heavier ethylene oxide based Ethyl diglyme available commercially.
Glymes
Ethyl diglyme, or glymes, are aprotic, saturated polyethers that offer high solvency, high stability in strong bases and moderate stability in acid solutions. Ethyl diglyme efficiently solvate cations, increasing anion reactivity, and thus can increase both selectivity and reaction rates. Most Ethyl diglymeare water-soluble, but a range of solubility and boiling points are available. The polyether structure produces only weak associations between glyme molecules, and is responsible for the low viscosity and excellent wetting properties of these solvents. A further structural feature of Ethyl diglyme that contributes significantly to their usefulness involves the arrangement of oxygen atoms, as ether linkages, at two-carbon intervals. The model of the Ethyl diglyme molecule (picture above) illustrates this periodic recurrence of oxygen atoms separated by two carbon atoms. This steric arrangement, analogous to that of crown ethers, gives Ethyl diglyme the ability to form complexes with many cations. Glycol diethers have a wide range of solubilities and boiling points. They are used as reaction solvents and in closed loop applications such as gas scrubbing and in refrigeration systems. The higher molecular weight Ethyl diglyme beginning with ethyl diglyme are suitable for emissive applications such as coatings, inks, adhesives and in cleaning compounds. The lower molecular weight Ethyl diglyme should not be used in emissive applications due to their reproductive toxicity.
Pharma and fine chemicals synthesis of Ethyl diglyme Due to their high stability and solvency, Ethyl diglyme are widely used as reaction media for processes involving alkali metal hydroxides, sodium hydride, and alkali metals. Grignard reaction yields can be increased and purification costs reduced by using Ethyl diglyme as reaction solvents. Sodium borohydride at high temperature can be substituted for lithium aluminum hydride in some reductions. Carried out in Ethyl diglyme sodium aluminum hydride can be prepared directly from the elements in Ethyl diglyme. Ethyl diglyme is the solvent of choice when preparing aryl sulfides via use of sodium tetrafluoroborate as a catalyst. Ethyl diglyme is also a key to the efficient synthesis of the anti-AIDS drug Nevirapine. Preparation of urethanes, hydrogenations, condensations, oxidations, olefin insertions, oligomerizations of olefins, and addition reactions can be carried out in Ethyl diglyme as reaction medium.
Ethyl diglyme are also useful as solubilizing agents, extractants and selective solvents. Methoxyacetaldehyde dimethylacetal can be prepared by electrochemical oxidation in Ethyl diglyme. Aspartame was prepared by enzymatic catalysis in triglyme-water medium.
Polymerization and polymer modification of Ethyl diglyme
Catalysts of the Ziegler-Natta type for the polymerization of alpha-olefins are advantageously prepared as a slurry incorporating Ethyl diglyme. Ethyl diglyme are additionally useful in removal of unreacted monomer in this type of polymerization. When Ethyl diglyme is used to modify the Ti-AI-catalyzed preparation of a block ethylene-propylene copolymer, the physical properties of the copolymer are greatly improved. Similarly, conjugated dienes can be polymerized in the presence of metal-based catalyst mixtures containing Ethyl diglyme. Catalyst solutions for other types of polymerization advantageously use Ethyl diglyme. Monomers polymerized in the presence of Ethyl diglyme include cyclosiloxanes, conjugated alkadiene, lactams, dicyclopentadiene, vinyl chloride, fluorinated acrylic esters and 1-octene. Ethyl diglyme are also useful in formulating
storage-stable vulcanizing agents for urethane rubber. Polyethylene terephthalate (PET) and its copolymers are produced with improved properties by incorporating Ethyl diglyme into the finished product.
Ethyl diglyme are useful in formulating rigid polyurethane foams with improved fluidity during molding and with improved bonding strength. The viscosity of polyols useful in the manufacture of polyurethanes can be reduced by means of Ethyl diglyme without adversely affecting physical properties. Polyurethane coatings used to form pinhole-free films with good adhesive strength, applicable to electrical and
electronic parts, utilize Ethyl diglyme. Isocyanates are processed and formulated using Ethyl diglyme to yield isocyanurate and polyisocyanate prepolymers used in various polyurethane applications.
Gold refining of Ethyl diglyme
Ethyl diglyme is a selective solvent for the extraction of gold from hydrochloric acid solutions containing other metals. Treatment of the extract with a reducing agent such as oxalic acid reduces the trivalent gold to gold powder.
Ethyl diglyme have the following high-performance properties:
Dissolve polar and non-polar contaminants
Very low odor compared to esters, ketones and monoethers
Choice of boiling point
Fully compatible with quats
Compatible with hydrocarbons AND water!
Run cleaning hot or cold and match requirements for solvent recovery
Use of higlyme (non-VOC) for heavy-duty water-based cleaning solutions
Optimized cleaning by using Ethyl diglyme for more polar impurities
Use of Ethyl diglyme for non-polar impurities and high temperature
Maintain ability to remove metal ions
Reduce surface tension
Toxicity of lower Ethyl diglyme Monoglyme, Ethyl diglyme and ethyl glyme are only suitable for use in enclosed applications such as reaction solvents as they are recognized reproductive toxins. Higher Ethyl diglymes, such as ethyl diglyme, Ethyl diglyme, tetraglyme, polyglyme and higlyme have lower acute and reproductive toxicity and are considered suitable for use in emissive applications.
Ethyl diglyme is most commonly utilized as a high-performance solvent for both laboratory and industrial applications. It effectively solvates digital inks and decorative ceramic inks, since Ethyl diglyme is stable enough to withstand the high temperatures of these applications. Ethyl diglyme is also commonly used on small scales as an extraction solvent for gold from hydrochloric acid media, a process which results in an extremely high concentration of pure gold metal.
Ethyl diglyme can also be used as an intermediate in the production of siloxane-based adjuvants.
Ethyl diglymeALSO KNOWN AS
dibutyl carbitol, dibutyldiglycol, diethylene glycol di-n-butyl ether, 2-butoxyethyl ether
PACKING INFO of Ethyl diglyme
Bulk tankers, totes, and drums
APPLICATIONS of Ethyl diglyme
Glycol ethers, with the combination of ether, alcohol and hydrocarbon chain in one molecule, provide versatile solvency characteristics with both polar and non-polar properties. The chemical structure of long hydrocarbon chain resist to solubility in water, while ether or alcohol groups introduce the promoted hydrophilic solubility performance. This surfactant-like structure provides the compatibility between water and a number of organic solvents, and the ability to couple unlike phases. Glycol ethers are characterized by their wide range of hydrophilic/hydrophobic balances. glycol ethers are used as diluents and levelling agents in the manufacture of paints and baking finishes. Glycol ether series are used in the manufacture of nitrocellulose and combination lacquers. They are used as an additive in brake fluid. They are formulated for dying textiles and leathers and for insecticides and herbicides. They provides performance in cleaners products with oil-water dispersions. They are used in printing industries as they have a slow evaporation rate. They are used as a fixative for perfumes, germicides, bactericides, insect repellents and antiseptic. They are used as an additive for jet fuel to prevent ice buildup. Thje term of cellosolve refers to Ethyl diglyme or a group of glycol ether solvent as below.
